Mastering The “I Haven’t Seen You In A While” Conversation

“Hey, Matt! Great running in to you. I haven’t seen you in a while! How have you been?”

“Oh no, not again. What do I say here? Is this really the moment he’s choosing to have this conversation? Does he seriously want a play-by-play recap of the last year of my life? No. It can’t be. He has Facebook. He knows the big stuff. He probably just wants to keep this interaction short and sweet. Or maybe he’s being genuine. He is my friend. Well, kind of. I think. Well, I like him. I want to know about his life. Sort of. But not here. Well, why not? We are at Wal-mart. Neither of us has anything that could melt. Do we go shopping together while we catch up. Two dudes. Two shopping carts. Catching up on life. That’s normal. Should we share a shopping cart? Would that be weird? Yes. Oh man, have I still not answered his question!”

Of all of the conversation types, the one that scares me the most is the “I haven’t seen you in a while. How’s life?” conversation. Why? Usually, this is a person I care about and genuinely like, but rarely see. Because I like them, I really want to engage in a friendly discussion. The problem is that I never run into these people at opportune moments. One of us is strapped for time. And because the odds of us running into one another again are slim, I feel pressure to cram 45 minutes of conversation into 45 seconds.

After crashing and burning enough times, I decided to come up with a plan. If you struggle with this type of conversation, let me offer some help.

The Purpose: Gauge Their Interest

The trickiest part about these conversations is gauging the level of interest of the other person. Are they being polite? Or do they really want to know about my life? And if so, how much do they want to hear? And since one of us is likely strapped for time, there is a limit to the amount of genuine-ness I can express.

Assuming that I actually like this person (if not, just end the conversation and be done), the trick is to discover their interest-level by answering the question with incrementally more detail. To do this, we need to plan ahead and formulate three different responses to the question “How’s life?”

Response #1: The 5-Second Answer

No one likes a long-talker. They suck the life out of any conversation by turning dialogs into monologues. Soliloquies are great for Shakespeare, but not for people who want friends. By planning our response to the “How’s life?” question, we avoid being a long-talker.

And to be honest, most people don’t care how we’re doing. They’re just being polite. By giving a 5-second answer to the question, we give our conversation partner an easy exit from the conversation and prevent a lot of anxiety on both ends.

The most useful 5-second answers are the ones with a little bit of thought. Here are some ways to be thoughtful about our 5-second answer. Make it good because you will say it a lot.

The spouse rule.

Our 5-second answer should not be so vague that a person needs to ask for clarification. It should be a stand-alone answer. Imagine that my friend is talking to his spouse later that night and is recounting this conversation. When the spouse asks, “How is Matt?” my friend should be able to satisfy his spouse’s curiosity with my 5-second answer and no more. If the spouse would need to ask for clarification, my answer was too vague.

Good: “It’s going well. I don’t know if you saw this on Facebook, but my brother just had a baby boy, so I am officially an uncle!”

Bad: “It’s going well. I’ve been spending lots of good time with family.”

Be positive.

If your life has been more tragic than comic lately, you do not have to fake a happy life. You do not have to be disingenuous. But our 5-second answer is not the place to reveal how painful our lives have been. Save that for later. Our 5-second answer should be light. Focusing on the future might help.

Good: “I’m doing well. The last few months have been weird, but I am going on a fishing trip with my dad next month up in Wisconsin, which will be awesome.”

Bad: “Not well. My mom passed away a few months ago.”

Talk about what you want to talk about.

Our 5-second answer should set the tone for a conversation we would enjoy having, should they ask us to elaborate. So if we don’t want to talk about work, we won’t bring it up.

Good: “I’m doing well. Life hasn’t been quite as interesting since I got a promotion, but I did recently start taking boxing lessons, which is a welcome change of pace.”

Bad: “I’m well. Just got a promotion at work!”

Things to avoid.

Don’t use the word “busy.” The weather is not interesting. Don’t lead with football.

What is your 5-second answer? (Yes, it’s totally legal for me to ask you to stop and think while you’re reading an article. So stop right now at this moment in history and write down one or two good 5-second answers.)

Response #2: The 30-Second Answer

After we have given our 5-second answer, the trick is to be selective about who gets the 30-second answer. Not everyone wants to hear it. Some people just want a few seconds of small talk. How do you decide?

Only give the 30-second answer to people who ask an open-ended question.

Let me give you an example:

Hey, Matt! Lucky running in to you. It’s been a while. How’s it going?

Hey! It’s going well. I don’t know if you saw this on Facebook, but my brother just had a baby boy, so I am officially an uncle!

Oh, cool! I bet that’s exciting for you.

Absolutely. It’s so fun. I’ve taken way too many pictures.

Haha! Do they live close? Have you visited them much?

Yep. At least once a week.

Just make sure you don’t visit too much! When we had our daughter our family couldn’t leave us alone!

I bet that’s miserable. Haha! How are you?

Notice in this conversation that the person isn’t asking for more information. There are no open-ended questions. They are actively keeping the conversation in 5-second-answer territory. There’s nothing wrong with that. We can have a fun conversation without going too deep. As long as we give them something to take home to their spouse, we’ve done well. Ask them about their life and transition out of the conversation.

If they do ask an open-ended question, like, “Has that been exciting for you?” or “What’s the best part of being an uncle?” that signals that they are interested in your 30-second answer.

Now, you don’t need to script your 30-second answer, but it helps to have a few thoughts ready to share.

Stay on-topic.

Remember your 5-second answer. This is the topic. The 30-second answer should not introduce new topics. You can do that later. Go deep, not wide.

Drop hints.

The 5-second answer is meant to provide a short, satisfying answer that will appease a spouse. It gives someone enough information about your life that you can end a conversation quickly, if needed. The 30-second answer is meant to gauge someone’s interest in your life. It’s kind of like fishing bait. If they take the bait, it opens up the conversation to more depth.

So give them a cliffhanger. Start an interesting story and see if they want to hear the end. Throw in a few short, interesting details that will make them want to ask for more. If they are genuinely interested in your life, they will pick up on these hints. If not, end the conversation.

Don’t forget to ask about their life.

A conversation is meant to be a dialog, not an interview. When you finish your 30-second answer, ask them a thoughtful question. Remember that you probably like this person.

What is your 30-second answer? Again, take a few minutes (right now!) to write down the bullet points of your 30-second answer. Remember to stay on topic, but to add-in the beginning of a few juicy details.

Response #3: The 2-Minute Answer

Remember how the initial question was “How are you?” Now is the time to actually answer that question. If someone picks up on some of the hints you dropped in your 30-second answer, it means that they are hoping to have a more genuine conversation with you. Now is the time to give them the longer answer. If they did not pick up on the hints, stay in Small Talk Land and end the conversation as soon as you feel comfortable.

I don’t have any tips for your 2-minute answer (other than to keep it under two minutes). I just recommend that you think about it.

How has your life been? What are you thinking about? What has been difficult? What has been exciting?

Now is not the time to externally process all of these questions. Your 2-minute answer should be the fruit of your reflection, not the time to do so.

If you haven’t taken time this month to reflect on your life, do that soon. Or now. Actually, do it now. If you and I were having this conversation, what would be the bullet points of your 2-minute answer?

What next? Continue the conversation later.

OK, so you run in to an old friend at the grocery store. You are both excited to see one another. He asks the “How’s life?”question. You give him your 5-second answer. He wants to hear more. You give him your 30-second answer. You ask him some questions. He keeps asking thoughtful questions, so you decide to give him your 2-minute answer. It’s been about five minutes. You ask a few thoughtful questions. He talks for a minute or two.

At this point, your conversation should end. You have groceries to buy. No matter how much you want the conversation to continue, cut it off.

Why? There are better contexts to catch up with old friends. Instead of over-milking this encounter, invite him to lunch. Buy him coffee. Continue the conversation another time.

Granted, very few “How’s life?” conversations will progress this far. Most of the time, someone will tap out of the conversation. That’s fine. Save the coffee dates for the genuinely interesting people with whom you don’t have natural opportunities to connect.

Closing

Running into an old friend or a casual acquaintance shouldn’t be stressful. With a little preparation and thought, you can prepare for these encounters and help them go as smoothly as possible. And just because you’re preparing for these interactions doesn’t mean that they’re fake. Practicing the art of conversation doesn’t make it any less genuine. On the contrary, giving some thought to your answers guarantees that they will be more genuine.

So what will you say the next time you run into an acquaintance? Do you have your 5-second, 30-second, and 2-minute answers ready to go?

Matt

Tired of the low expectations that accompany being a millennial?

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